In my experience, it isn't too hard to find a Regents roommate. I found my roommate for 1L year through a post on the admitted student's board. Alternatively, if you come to ASW, you can meet other soon-to-be 1Ls there and probably find a willing roommate.

I would recommend not living in Regents if you'd really prefer to live by yourself. Yes, many law students live there, and it's easy to find a roommate, make friends, etc. But if you don't want a roommate, you can find relatively inexpensive (and large) studios through U of C grad student housing that are on the same bus route. Save money, live like an adult, maybe even meet some non-law/medicine/business school students. Regents has well-documented internet & cable TV problems. People complain about the management constantly. You have to pay extra to use the gym, and oh yeah--Obama won't be working out there anymore.

Eh, didn't mean to insult. Live like an adult = just, you know, have your own bathroom & kitchen. For the record, most Regents dwellers are eminently mature. But if you've been used to living on your own post-undergrad, you may feel more comfortable elsewhere. If people don't agree Regents is a rip-off, feel free to argue the other side. I'm repping the grad housing because I heard very little about it when I came to U of C, but tons of students from other programs live there and it's a decent option.

The 1Ls in Regent's are also too clique-based for my tastes, IMO. I always see the same people in the Lounge, studying together, eating together, and even sleeping together. I can walk in at any time of day and see the same five people near each other. The incestuousness is disgusting. I've stopped hanging out with the New Grad people for the same reason.

Live alone and meet a whole host of different people. If I could do it over, that's what I would have done. Apartments in Hyde Park are cheap and you'll be a much healthier person. It's even better if you have a long-term girlfriend or boyfriend to cook for you when you're bummed out or busy.